The Chicago (originally Calumet) Skyway is a 7.8-mile long
Expressway
connection between the Dan Ryan Expressway and the Indiana
Toll Road,
including a high-level bridge over the
Calumet River.

When the terminus of the Indiana Toll Road was set at 106th Street and Indianapolis Boulevard, a diagonal route, adjacent to the Pennsylvania and New York Central
Railroad
embankments, was approved in 1954. Construction began in 1956 and the toll road opened in April 1958.

State law did not permit cities to build toll roads, so legally the facility is a toll bridge with long approaches. Traffic counts fell far short of projections as motorists used toll-free I-94 instead, and for decades the city was unable to repay the revenue bonds, even as tolls increased from twenty-five cents to two dollars. The roadway became self-sustaining in 1989 and was rehabilitated in the late 1990s.